반응 #4896

반응 방정식

Hydrogen chloride

sodium 2-[(1-methyl-3-pyrrolidinyl)oxy]-3-pyridinecarboxylate

triphenylphosphine

carbon tetrachloride

→

2-(2-Chloroethyl)-2,3-dihydro-4-methylpyrido[3,2-f][1,4]-oxazepin-5(4H)-one hydrochloride

용매

chloroform

ethanol

반응 조건

후처리

1. 1
   온도at reflux for 1.5 hr
2. 2
   기타the heat removed
3. 3
   workup.STIRRINGThe solution was stirred for 1 hour
4. 4
   온도while cooling
5. 5
   workup.ADDITION200 ml of isooctane was added
6. 6
   추출The solution was extracted 4 times with a total of 800 ml of dilute hydrochloric acid
7. 7
   추출extracted with chloroform
8. 8
   기타The chloroform layer was separated
9. 9
   건조dried over sodium sulfate
10. 10
    농축concentrated
11. 11
    workup.DISSOLUTIONThe residue was dissolved in a mixture of 500 ml each of isopropyl alcohol and isopropyl ether
12. 12
    기타A portion was recrystallized from isopropyl alcohol, m.p. 149°-153° C.

실험 절차

Hydrogen chloride gas was bubbled into a suspension of 150 g (0.61 mole) of sodium 2-[(1-methyl-3-pyrrolidinyl)oxy]-3-pyridinecarboxylate in 1 liter of chloroform until a pH of 6 was reached. To the stirred mixture was added 350 g (1.34 mole) of triphenylphosphine and 350 g (2.3 mole) of carbon tetrachloride and the resulting cloudy solution was stirred at reflux for 1.5 hr. About 100 ml of ethanol was added and the heat removed. The solution was stirred for 1 hour while cooling and 200 ml of isooctane was added. The solution was extracted 4 times with a total of 800 ml of dilute hydrochloric acid. The acid extracts were combined, made basic with sodium hydroxide and extracted with chloroform. The chloroform layer was separated and dried over sodium sulfate and concentrated. The residue was dissolved in a mixture of 500 ml each of isopropyl alcohol and isopropyl ether and acidified with ethereal hydrogen chloride. The resulting crystals weighed 82 g (49%). A portion was recrystallized from isopropyl alcohol, m.p. 149°-153° C.

출처